


Darkest Hell

by entropicangels (ce_reads1996)



Category: Supernatural
Genre: Aftermath of Torture, Alastair (Supernatural) Being an Asshole, Blood and Torture, Dean Winchester Dreams, Dean Winchester Dying and Coming Back to Life, Dean Winchester is Protective of Sam Winchester, Dean Winchester is Tortured in Hell, Gen, Implied/Referenced Torture, Psychological Torture, Season 3 Finale, Season 4 spoilers-ish, Season/Series 03, gets a bit torture porny
Language: English
Status: In-Progress
Published: 2014-10-19
Updated: 2015-01-13
Packaged: 2019-10-23 02:00:08
Rating: Mature
Warnings: Graphic Depictions Of Violence, Major Character Death
Chapters: 4
Words: 2,289
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17674271
Author URL: https://archiveofourown.org/users/ce_reads1996/pseuds/entropicangels
Summary: The events of the day Dean Winchester died were hard to forget. The hellhounds ripping at him, tearing him almost in two, was the worst pain he had ever felt.Now his deal had caught up to him. Now he was in Hell, being tortured within an inch of his undead life. The only solace he had were dreams of his brother and the life up above the deep dark pit.





	1. Year 1

Pain. That is all the feeling that Dean Winchester could feel. His skin felt as if it was aflame; he was smouldering from the inside out.

Dean peeled open his eyes. A horrible stench of rotting flesh filled his nostrils. He choked on a deep breath. There was darkness all around him; as his eyes adjusted to the dark, he realised he was chained so he couldn’t move. He was wearing scratchy pants that rubbed his skin rough whenever he moved. Dean pulled at his restraints, but they wouldn’t give.

After what seemed like hours, a single light flickered, coming from a bulb on a string that seemed to go up into darkness. Dean could just barely make out his surroundings. He was stretched out vertically on a podium, chains wrapped around his wrists and ankles yanking taunt.

Suddenly, he heard screaming. Heart-wrenching, stomach-churning, painful screaming. It cut through the still and silent air like it was gunning for him. Abruptly, the screaming was slowly cut off by a wet choking sound. The victim was drowning in his own blood.

Afterwards, the silence was all there was. It was so silent that Dean could hear his own ragged breaths and the clink of chains as he struggled.

Footsteps. Slowly, but getting closer and closer towards Dean. The hair on the back of his neck stood on end, and he shivered involuntarily. Soon, he could see a dark figure just beyond the view of the flickering light.

The figure stepped into the light; a skeletally thin man with a beard and a black suit. Blood was splattered on his grinning visage.

“I do apologize, my prior client was a bit…uncooperative,” said the man, his voice soft and smooth. He pulled out a handkerchief and almost daintily wiped the blood from his face.

“Where am I?” asked Dean, his voice hoarse from disuse.

“Ah, the cliché. ‘Where am I? Who are you? What do you want?’ Well, I’d hate to break it… no, I’d love to break it to you. You’re in Hell,” said the Man, delicately folding his handkerchief and placing it back in his suit jacket pocket.

It all came flooding back to Dean. Sam, Ruby’s vessel a.k.a Lilith, and the hellhounds. He could still feel as if they were clawing at his insides, shredding his very being. The worst part was seeing Sammy’s face.

            “No witty retort this time Dean-o?” the man, presumably a demon, chuckled. “My, my. I forgot my manners, the name’s Alastair. I’m here to look after you for…all eternity.”

            “Bring it on, chuckles,” Dean spat, pulling at his chains so they jangled loudly.

            “There’s your sense of humour. You won’t be laughing for long,” Alastair purred. He stretched out his right arm and a chain appeared, wrapping around it. He took the hook at the end of the chain in his hand, and stared at it, almost admiringly. Alastair grinned even wider as he fingered the sharp point of the chain.

            “This is gonna be fun,” he said, walking closer to Dean.

            Dean’s chest heaved. For the first time in a long time, he was frightened.

            “What’s the matter, dearie? You’re shaking like a leaf,” Alastair chuckled.

            “Go to Hell,” Dean sputtered, his voice shaking.

            Alastair let out a huge laugh. “We’re already here,” he said darkly, taking the metal hook in his fist and using the sharp point, dug it into Dean’s side.

            Through clenched teeth Dean screamed, throwing his head back and struggling. He felt the hook pierce through the first few layers of his skin and push deeper until it came out the other side. Blood dribbled thickly out of the wound. Sweat ran into his eyes; his left side was exploding with pain.

            Through ragged breaths, Dean said, “Is that all you got?”

            Alastair smiled. “We’re just getting started.”

***

             _“Dean?”_

_Darkness filled his vision. His ears pricked up. Sammy?_

_“Oh my god, Dean!” Sam said, and Dean felt hands touch his face._

_“Sammy…” Dean said weakly._

_“You’re alive! We have to get out of here!” Sam said, sternly._

_“You…you can’t be here,” Dean said._

_“I found a spell, now we only have a few minutes…” Sam said, pulling at the chains that held Dean in place._

_“Sammy, I—“ Dean choked._

***

            Dean opened his eyes once more. Sam was gone. Pain filled his whole body.

            “No! No!” he screamed.

            Lightning crashed and thunder rumbled.

            “Somebody help me!” he yelled, blood filling his mouth and tears streaming down his face. “Sam! SAM!”

            No one answered his call.


	2. Year 2

Dean felt himself slowly rise from unconsciousness, his body whole and new again. There was no trace of the previous tortures that Alastair had inflicted on him; the hook and chain piercing through his sides and the meat of his shoulder. He had almost gotten used to the pain of it, which was surprising. What he had gotten used to was saying no.

***

Dean let out a scream of pain, his breath coming out in ragged intervals. He figured he had about six months of this indescribable pain.

“So, Dean. Will you pick up the knife? Join me in torturing souls?” Alastair inquired, grinning like he had stapled his cheeks together.

“Go screw yourself,” Dean spat, spewing blood all over Alastair’s face.

Alastair’s grin shifted slightly as he took out his black, satin handkerchief and wiped the blood from his face.

***

Dean’s mind went back to reality and he saw Alastair standing before him, the same smug-ass grin on his face.

“Have you ever heard of the myth of Prometheus?” he asked, slowly pacing in front of Dean.

“Can’t say I have,” Dean replied, just waiting for him to get on with it.

“Prometheus’ misdeeds towards Zeus landed him in Hades, where his punishment was that he was chained to a mountain peak and every day an eagle tore at his body, consuming his liver. And the next day, his liver would grow back and the punishment would start all over again.”

“Your point is?” Dean said, snarkily.

“I thought I would plagiarize his idea,” Alastair grinned.

Alastair stretched out his arm and black smoke formed a tornado, and when it cleared, there perched a crow with bright, red eyes.

The crow flew towards Dean, scanning his body for a moment and then pecked at his chest. With its talons, it tore at his stomach, shredding the flesh to ribbons.

Dean screamed and tried to twist himself away from the bird, but it flew ever closer, pecking and tearing. He could feel his insides pouring out of the now gaping hole in his stomach.

As Dean was passing out, all he could hear was Alastair’s throaty, hearty laugh.


	3. Year 7

Seven years. That was how long Dean had endured countless amounts of torture. Alastair was being more and more creative with each passing year.

***

Twelve Months Ago

“Wakey, wakey, Sleeping Beauty,” Alastair said, touching a cool blade to Dean’s face.

Dean groaned. “What’s on the menu for today, Alastair? Burning? Flaying? Taping my eyes open and making me watch gay porn?”

Alastair chuckled. “Your ability to keep having a sense of humour amazes me, Dean.”

“Yeah, me too.”

“Let’s get started, shall we? You know, since it’s the New Year, I’ve made a New Year’s…resolution you could say,” Alastair said.

“Oh, yeah? What is it? Putting on some muscle?” Dean smirked.

“Oh, this form isn’t buff enough for you? You should see my true form,” Alastair chortled. “No. I’ve made the resolution to be a bit more…” he rubbed his thumb on the edge of the blade. “Slice and dice,” he finished.

With a small flourish, he started towards Dean and gripped Dean’s left ear with his free hand and sliced it clean off with the other.

Dean shrieked in pain, feeling hot blood run down the left side of his neck. He was still chained to the podium, so he couldn’t staunch the bleeding.

Alastair stood back, a bit farther from Dean, admiring the appendage he had just cut off.

“Let’s see how you feel without fingers and toes,” he said, tossing the ear aside and stepped towards him, bloody knife raised.

***

Miraculously, just as his body had healed every other day, his ear, fingers and toes had all grown back as he slept, ready for another day’s torture.

“Morning, Dean,” Alastair breathed, almost a whisper as he appeared before Dean, with iron stoking a fire.

“Great. Are you going to brand me as Hell’s bitch?” Dean asked, choking on the smoke.

Alastair smiled. “You could say that.”

“Oh goody,” Dean said, sarcastically.

Alastair stopped stoking the fire. “Is this getting too boring for you Dean? You could always stop fighting it. Pick up the knife, join me in torturing souls.”

“Not a chance, chuckles,” Dean replied, stretching.

Alastair examined the pointed tip of the iron. It glowed white-hot. “Pity,” he spat.

He slashed Dean with the iron. Dean almost threw up as he heard the sizzle of his own flesh. Dean drifted off, ready to escape.

***

When Dean opened his eyes, he could feel the cool night breeze on his face. The clusters of stars shined above him; the first natural light he has seen in years. He was sitting on the hood of the Impala; he rubbed his hand on the smoothness of her. He remembered this, it was right after they killed that Rugaru.

“Dean?” said a voice.

He turned towards the voice. It was Sam, holding out a cold one for him.

“Sammy?” Dean asked, staring into those questioning hazel eyes.

“Please don’t call me that,” Sam said as Dean took the beer bottle and cracked it open.

The cool liquid passed his lips and Dean sighed.

“Bitch,” Dean jested.

“Jerk,” Sam replied.


	4. Year 20

The daily grind was slowly getting too much for Dean. Alastair would torture him in seemingly imaginative and inventive ways, making him feel pain in places that he hadn’t thought he could feel pain in. Alastair would keep him awake for as long as he could, but even he wouldn’t dare try and make Dean feel less pain. It wasn’t in his nature.

Dean forced himself to bear the pain, only so he could be sucked back into the darkness of sleep. So he could see Sam again. He knew it wasn’t actually his brother, just some remnants of memories of him. But that didn’t matter. The fact that he could even remember him, even a little bit, meant that he had some scrap of hope. Hope that Sam would be still long above the heat and fire, even going back to Stanford.

Dean could imagine him in his dorm room, turning pages of law books, expectant for someone, some nice girl, to arrive. There would be a knock at the door, and Sam would slam his book shut, a giddy smile appearing on his face. Today was the day he was going to tell her that he loved her. 

He would stop for half a moment in front of a mirror, wrinkling his brow as he does, and running a hand through his hair. He would undo one button on his shirt, maybe two, and take a deep breath.

He would open the door, grinning even though his cheeks were bursting. But the smile slowly slipped away and Sam backed into his room, shaking his head. No, no! It was Alastair, forcing Sam backwards. This isn’t supposed to happen. Sam was supposed to have a normal, apple pie life. This isn’t right.

Grinning viciously, Alastair slashed at Sam’s torso, with a knife that seemed to appear in his hand. There was a small squelch as cloth and flesh tore. Blood started running from the wound. Sam was taken off guard then, hand moving to cover his wound, mouth agape.

Alastair took this as his chance and swept Sam’s feet out from underneath him and Sam crashed backwards to the ground. Alastair pounced and cut and slashed every piece of Sam he could find, slowly, so he could hear him scream. Why wasn’t anybody hearing this? Why wasn’t somebody rushing in the room?

“Stop…please…” Sam sputtered, trying to push Alastair off of him. Every part of Sam was now in pain, and he felt his energy slowly seeping out of him.

He could barely move. There must have been something on that blade. Something that was paralysing him.

His arms flopped uselessly to his sides and his head lolled to his left.

“No…” he slurred.

Sam saw out of the corner of his eye Alastair wiping his blade on Sam’s shirt, standing up and leaving, his job well done.

He watched as his blood dripped and gushed out of his many wounds. He knew he didn’t have the strength to call out, so it was certain he would lay there bleeding to death.

“Dean…”

***

“NO!” Dean screamed as he woke.

Alastair broke into a fit of laughter. “Have a nice dream?” He asked.

“Sam,” he sputtered, shaking. He looked around at his surroundings. It was the same dark room he had been in for twenty years. He was still in hell. “A dream?”

Alastair dramatically sighed, “Yes, Dean. Just a dream, as far as I know, your Sammy is fine and dandy. For now. I thought it would be more interesting just to take a sneak peek inside that noggin of yours.”

“And mess with my head?” Dean spat.

“Yes. Thought I’d try including some emotional torture in our lineup. I think we should try this again sometime. It worked especially well.”

“Screw you.”

“After all our time together, I thought you’ve developed some manners.”

“Apparently not,” Dean replied, shifting in his restraints.

“Let’s see if we can change that,” Alastair said.


End file.
